N,3-dimethyl-4-(piperazin-1-yl)benzamide dihydrochloride → 4-(4-((8-Ethoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N,3-dimethylbenzamide

HRID 1184516Notes

Reaction equation

HRID 1184516 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=2[CH:7]=[C:6]([CH:16]=O)[CH:5]=1)[CH3:2].Cl.Cl.[CH3:20][NH:21][C:22](=[O:36])[C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[C:25]([CH3:35])[CH:24]=1>>[CH2:1]([O:3][C:4]1[C:9]2[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=2[CH:7]=[C:6]([CH2:16][N:32]2[CH2:31][CH2:30][N:29]([C:26]3[CH:27]=[CH:28][C:23]([C:22]([NH:21][CH3:20])=[O:36])=[CH:24][C:25]=3[CH3:35])[CH2:34][CH2:33]2)[CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 66775618N,3-dimethyl-4-(piperazin-1-yl)benzamide dihydrochlorideHCID 718134828-Ethoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

Product 1

HCID 667169324-(4-((8-Ethoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N,3-dimethylbenzamide

Procedure

Using 398B and N,3-dimethyl-4-(piperazin-1-yl)benzamide-2HCl in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (t, J=6.95 Hz, 3H) 1.41 (d, J=6.82 Hz, 3H) 2.26 (s, 3H) 2.52-2.57 (m, 4H) 2.75 (d, J=4.29 Hz, 3H) 2.89 (br. s., 4H) 3.42 (s, 2H) 4.04 (d, J=7.07 Hz, 2H) 4.55-4.65 (m, 1H) 6.52 (s, 1H) 6.63 (s, 1H) 7.03 (d, J=8.34 Hz, 1H) 7.58-7.67 (m, 2H) 8.24 (d, J=4.04 Hz, 1H) 10.57 (s, 1 H). ESI-MS: m/z 453.4 (M+H)+. mp 173.4-180.5° C.

Sources & evidence

ORD record
ord-9b99e94aad9545208a97f1c0764bf94a
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

Loading…